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Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library

Storr, Thomas E.; Cully, Sarah J.; Rawling, Michael J.; Lewis, William; Hamza, Daniel; Jones, Geraint; Stockman, Robert A.

Authors

Thomas E. Storr

Sarah J. Cully

Michael J. Rawling

William Lewis

Daniel Hamza

Geraint Jones

Robert A. Stockman



Abstract

The application of a tandem condensation/cyclisation/[3+2]-cycloaddition/elimination reaction gives an sp3-rich tricyclic pyrazoline scaffold with two ethyl esters in a single step from a simple linear starting material. The successive hydrolysis and cyclisation (with Boc anhydride) of these 3-dimensional architectures, generates unprecedented 16-membered macrocyclic bisanhydrides (characterised by XRD). Selective amidations could then be achieved by ring opening with a primary amine followed by HATU-promoted amide coupling to yield an sp3-rich natural product-like library.

Journal Article Type Article
Publication Date Jun 1, 2015
Journal Bioorganic and Medicinal Chemistry
Print ISSN 0968-0896
Electronic ISSN 1464-3391
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 23
Issue 11
APA6 Citation Storr, T. E., Cully, S. J., Rawling, M. J., Lewis, W., Hamza, D., Jones, G., & Stockman, R. A. (2015). Combining two-directional synthesis and tandem reactions. Part 21: Exploitation of a dimeric macrocycle for chain terminus differentiation and synthesis of an sp3-rich library. Bioorganic and Medicinal Chemistry, 23(11), https://doi.org/10.1016/j.bmc.2014.12.050
DOI https://doi.org/10.1016/j.bmc.2014.12.050
Keywords sp3-rich; Natural product-like; Scaffold; Cycloaddition;
Two-directional; Macrocycle; Library; Tandem
Publisher URL http://www.sciencedirect.com/science/article/pii/S0968089614009080
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc-nd/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc-nd/4.0





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